Looking for the perfect blend of small-town charm and upscale comfort? Welcome to The Jackson, a boutique hotel in Woodstock, Vermont, where timeless design and thoughtful details create a stay that feels both cozy and elevated.
Boutique Comfort with Heritage Charm
Set on a quiet hilltop just minutes from downtown, The Jackson is a beautifully restored 16-room hotel that captures the spirit of Vermont hospitality with every detail. From curated furnishings to plush bedding and elegant finishes, each room feels like a private retreat.
Whether you’re here for a ski weekend, a summer hike, or a foliage-filled escape, The Jackson offers a warm landing spot after your day’s adventures.
Oakes & Evelyn: Elevated Dining, Right Downstairs
Your stay comes with more than just a beautiful room. Oakes & Evelyn, our on-site restaurant, brings a fresh take on Vermont flavors with a menu that’s seasonal, shareable, and simply delicious.
Guests and locals alike are raving:
“Exactly what Woodstock needed—cozy, elevated, and so good.”
“The vibe was spot on. Great cocktails, amazing shareables, and perfect martinis.”
Whether you’re grabbing a cocktail at the bar or settling in for a relaxed dinner, O&E brings a refined, welcoming energy to The Jackson experience.
Perfectly Placed in Woodstock, VT
Just steps from downtown Woodstock and a short drive to Killington and Saskadena Six, The Jackson puts you close to everything:
- Covered bridges
- Local shopping and galleries
- Scenic hikes and swimming holes
- Ski resorts and snowshoe trails
- Iconic New England charm in every direction
Why The Jackson Is the Top Luxury Hotel in Woodstock VT
Stylish, uniquely designed rooms
Direct-to-room check-in (no front desk hassle)
On-site restaurant and bar
Close to outdoor adventure and village life
Quiet, comfortable, and always welcoming
Plan Your Cozy Luxury Getaway
Whether you’re escaping from the city, planning a romantic weekend, or exploring the best of Vermont with friends, The Jackson is where cozy meets luxury in one of New England’s most iconic towns.
